Martinet dioxindole synthesis

The Martinet dioxindole synthesis is a chemical reaction used to synthesize dioxindoles 3 from anilines and esters of mesoxalic acid 1.[1][2]

Reaction mechanism

Heating a N-substituted aniline in the presence of an ester of mesoxalic acid 1 will produce the dioxindole 2. Heating of 2 in the presence of water will hydrolyze the remaining ester, and effect a decarboxylation to give the desired dioxindole 3.

References

  1. ^ Guyot, A.; Martinet, J. Compt. Rend. 1913, 156, 1625.
  2. ^ Sumpter, Ward C. "The Chemistry of Oxindole" Chem. Rev. 1945, 37, 443–479. (doi:10.1021/cr60118a003)

See also